Short synthesis of 3-(hydroxymethyl)xylitol and structure revision of the anti-diabetic natural product from casearia esculenta

Ruomeng Wang; Michael N. Paddon-Row; Michael S. Sherburn

doi:10.1021/ol402740m

Short synthesis of 3-(hydroxymethyl)xylitol and structure revision of the anti-diabetic natural product from casearia esculenta

Ruomeng Wang, Michael N. Paddon-Row, Michael S. Sherburn^*

^*Corresponding author for this work

Research output: Contribution to journal › Article › peer-review

8 Citations (Scopus)

Abstract

3-(Hydroxymethyl)xylitol, a compound reportedly isolated from the root of Casearia esculenta (Roxb.), along with its three possible stereoisomers, has been synthesized for the first time by way of a triple dihydroxylation reaction performed upon the simplest cross-conjugated hydrocarbon, [3]dendralene. The data for the natural product do not match any of the isomeric 3-(hydroxymethyl)pentitols. The structure of the natural product from the root of Casearia esculenta (Roxb.) has been corrected by reanalysis of the published data.

Original language	English
Pages (from-to)	5610-5612
Number of pages	3
Journal	Organic Letters
Volume	15
Issue number	21
DOIs	https://doi.org/10.1021/ol402740m
Publication status	Published - 1 Nov 2013

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N2 - 3-(Hydroxymethyl)xylitol, a compound reportedly isolated from the root of Casearia esculenta (Roxb.), along with its three possible stereoisomers, has been synthesized for the first time by way of a triple dihydroxylation reaction performed upon the simplest cross-conjugated hydrocarbon, [3]dendralene. The data for the natural product do not match any of the isomeric 3-(hydroxymethyl)pentitols. The structure of the natural product from the root of Casearia esculenta (Roxb.) has been corrected by reanalysis of the published data.

AB - 3-(Hydroxymethyl)xylitol, a compound reportedly isolated from the root of Casearia esculenta (Roxb.), along with its three possible stereoisomers, has been synthesized for the first time by way of a triple dihydroxylation reaction performed upon the simplest cross-conjugated hydrocarbon, [3]dendralene. The data for the natural product do not match any of the isomeric 3-(hydroxymethyl)pentitols. The structure of the natural product from the root of Casearia esculenta (Roxb.) has been corrected by reanalysis of the published data.

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ER -

Short synthesis of 3-(hydroxymethyl)xylitol and structure revision of the anti-diabetic natural product from casearia esculenta

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